[6Z,9Z,14S,(+)]-14-Methyloxacyclotetradeca-6,9-diene-2-one

Base Information

Chemical Name:[6Z,9Z,14S,(+)]-14-Methyloxacyclotetradeca-6,9-diene-2-one
CAS No.:90192-94-2
Molecular Formula:C₁₄H₂₂O₂
Molecular Weight:222.327
Hs Code.:
Mol file:90192-94-2.mol

Synonyms:[5Z,8Z,13S,(+)]-13-Methyl-5,8-tridecadienolide;[6Z,9Z,14S,(+)]-14-Methyloxacyclotetradeca-6,9-diene-2-one

Suppliers and Price of [6Z,9Z,14S,(+)]-14-Methyloxacyclotetradeca-6,9-diene-2-one

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 3 raw suppliers

Chemical Property of [6Z,9Z,14S,(+)]-14-Methyloxacyclotetradeca-6,9-diene-2-one

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of [6Z,9Z,14S,(+)]-14-Methyloxacyclotetradeca-6,9-diene-2-one

There total 6 articles about [6Z,9Z,14S,(+)]-14-Methyloxacyclotetradeca-6,9-diene-2-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: (R)-oct-6-yn-2-yl (Z)-dec-5-en-8-ynoate

: 90192-95-3
(R)-(-)-13-Methyl-(5Z,8Z)-5,8-tetradecadienolide

: 90192-94-2
(S)-(+)-13-Methyl-(5Z,8Z)-5,8-tetradecadienolide

Guidance literature:: (R)-oct-6-yn-2-yl (Z)-dec-5-en-8-ynoate; With C₂₆H₃₀F₁₂N₃O₂W; In toluene; at 20 ℃; for 24h; Molecular sieve; Glovebox; Inert atmosphere;

With hydrogen; In methanol; for 2h; Overall yield = 90 %; Overall yield = 44 mg;
DOI:10.1002/chem.201304414

Reference yield:

: (S)-oct-6-yn-2-yl (Z)-dec-5-en-8-ynoate

: 90192-95-3
(R)-(-)-13-Methyl-(5Z,8Z)-5,8-tetradecadienolide

: 90192-94-2
(S)-(+)-13-Methyl-(5Z,8Z)-5,8-tetradecadienolide

Guidance literature:: (S)-oct-6-yn-2-yl (Z)-dec-5-en-8-ynoate; With C₂₆H₃₀F₁₂N₃O₂W; In toluene; at 20 ℃; for 24h; Molecular sieve; Glovebox; Inert atmosphere;

With hydrogen; In methanol; for 2h; Overall yield = 86 %; Overall yield = 40 mg;
DOI:10.1002/chem.201304414

Reference yield:

: 58944-42-6
hept-5-yn-1-ol

: 90192-95-3
(R)-(-)-13-Methyl-(5Z,8Z)-5,8-tetradecadienolide

: 90192-94-2
(S)-(+)-13-Methyl-(5Z,8Z)-5,8-tetradecadienolide

Guidance literature:: Multi-step reaction with 4 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -50 °C / Inert atmosphere

1.2: 2 h / 20 °C / Inert atmosphere

2.1: titanium(IV) isopropylate; N,N’-(1R,2R)-cyclohexane-1,2-diylbis(1,1,1-trifluoromethanesulfonamide) / toluene; hexane / 0.5 h / -78 - 40 °C

3.1: dmap / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

4.1: C₂₆H₃₀F₁₂N₃O₂W / toluene / 24 h / 20 °C / Molecular sieve; Glovebox; Inert atmosphere

4.2: Lindlar catalyst / 2 h

With titanium(IV) isopropylate; dmap; oxalyl dichloride; C₂₆H₃₀F₁₂N₃O₂W; N,N’-(1R,2R)-cyclohexane-1,2-diylbis(1,1,1-trifluoromethanesulfonamide); dimethyl sulfoxide; In hexane; dichloromethane; toluene; 1.1: |Swern Oxidation;
DOI:10.1002/chem.201304414